risk | Chase Jarvis

Oct 07

How ‘Playing It Safe’ Almost Cost Me Everything (Don’t Settle!)

Illustration of a person standing at the edge of a high cliff, gazing out over distant mountains under an orange sky, symbolizing contemplation, choice, and risk.

Read from "Never Play It Safe" (pg 11): I kept letting myself get talked out of living my dreams by people who had given up on theirs. And it became a pattern that I repeated well into adulthood. I’d discover something unique and different about myself that I truly loved—go deep into that thing that made me come alive—and then like clockwork I’d put someone else’s idea of what I should be doing above my... read more ›

675 reads

Sep 02

Why Success Demands You Never Play It Safe

Have you ever felt that gnawing sensation in your gut, telling you something isn't quite right? That voice whispering you're meant for more, even as you're ticking all the boxes of a "successful" life? I've been there. In fact, I was there just months ago, staring at the finished manuscript of my new book. By all accounts, it was a solid piece of work. But deep down, I knew it wasn't the book I needed... read more ›

487 reads

Aug 26

Why Playing It Safe Is Riskier Than You Think

READ THIS FIRST! Security is mostly a superstition. It does not exist in nature, nor do the children of men as a whole experience it. Avoiding danger is no safer in the long run than outright exposure. Life is either a daring adventure, or nothing. - Helen Keller View this post on Instagram A post shared by Chase Jarvis (@chasejarvis) Safety is an illusion. It does not exist in nature, so why then... read more ›

412 reads

Jul 29

Redefining Success: I Made $5 Million in Revenue and Still “Failed”

Redefining success through creative entrepreneurship. A man is deeply focused on a chess game, holding a piece above the board. The scene is bathed in dramatic lighting, casting strong shadows. The background features an abstract, gritty texture with predominantly red and dark tones, adding intensity to the image. The chess pieces and the board are in shades of blue and gray, contrasting sharply against the vibrant backdrop.

I was so wrong about what success really means in the startup world. It took me years to learn the importance of redefining success rather than following someone else's rules. For years, I prided myself on being someone who didn't know how to lose. Give me a game, and I'd find a way to win. I did this with sports, school, and even work. I was always good at figuring out how to come out... read more ›

189 reads

Sep 06

Why We Need to Talk About Failure with Amy Edmondson

Thomas Edison, Charles Darwin, Steve Jobs... humanity has seen quite a few failures over the years. But history doesn't remember them for their missteps - it's for what they accomplished in spite of all else. Beyond impressive inventions and firsts of their kind, people appreciate other people who show them what’s possible with the right mindset. Amy Edmondson, Novartis Professor of Leadership and Management at the Harvard Business School, has been studying the science behind... read more ›

1K reads

Aug 30

How to Make Money in An Economy That Hates You with Chris Guillebeau

To say the world today is uncertain would be an understatement. Almost nothing's guaranteed, and it seems like new disruptions to the status quo emerge every day. While our parents might have had the luxury of only worrying about how the rise of rap might impact their kids' future, our generation lives in a much different reality. The economy. Artificial Intelligence. Global conflict. Evolving standards of work. Pandemics. Cybercrime. The only certain thing there is... read more ›

1K reads

Jul 24

Manage Risk Like an Entrepreneur

In this episode, we dig into the importance of taking creative risks. We all know that some risk is necessary. Simply said, you cannot stand out and fit in at the same time. If you're not sharing your work, you're hiding, and this tends to compound on itself. Once you start hiding, you stop growing. Creativity requires taking risks and embracing failure. Failure is the forward propulsion toward success and the sooner we can change... read more ›

625 reads

Nov 28

What Price Are You Willing to Pay to Live Your Best Life

If you’ve been a long time listener of this show, you’ve heard me say “you can’t stand out and fit in at the same time. If you never make anything, if you make only what you’re comfortable making, or if you are making but you never share, you’re hiding. Once you start hiding, you stop growing. Part of you goes to sleep. Even as I reached what I thought was my creative zenith, it took... read more ›

907 reads

Oct 17

3 Ways to Keep Your Project Moving and Embrace the Unknown

Beginnings are tenuous times. Getting anything substantial off the ground means making countless tiny decisions first, any one of which might assume vast importance—if you’re successful down the road. Paralyzed by Fear & Decisions The danger is twofold. On the one hand, you can become paralyzed by all the decisions you need to make. They can steal the life from your project—whatever the medium and at whatever the scale—before you’ve even begun. “What if I... read more ›

989 reads

Aug 15

How Calculated Risks Expand Our Career Growth

If calculated risks keep us growing, why do we stop? There are two contrasting ideas that many of us have about creativity. It’s that we want to stand out and share our work while at the same time we want to fit in. When we stand out, it means we’re not fitting in. We can’t have both. Human nature likes us to fit in, so it becomes very risky behavior to stand out even in... read more ›

1.1K reads